Softener for halogen-containing high-molecular weight, organic compounds



Patented Sept; 22, 1942 PAT NT, OFF-ICE ."SOFTENEB FOBHALOGEN-CONTAINING HIGH-MOLECULAR v COMPOUNDS Max Biigemann, ColognNelles, Leverkusen-Schlebusch, signor's, by mesne assignments, to

Corporation, New York, N. Y.,

AnilineJzFilm WEIGHT, ORGANIC e-Mulheini. and Johannes s General acorporation of Delaware No Drawing. Application Apruis, mast-1.1P10468578. InGermany May a, ma

4 Claims. .(Cl. 260-36) The present invention relates to a new com--position of matter.

We have foundthat esters of ll-dialkylaminocarboxylic acids representvaluable softeners for high molecular halogen containing organiccompounds of the type of polyvinyl chloride, chlorinated rubber, mixedpolymerizates of vinyl chloride and other polymerizable substances suchas acrylic acid esters or 'vinyl esters, furthermore, products of thechlorination of polymeric butadiene hydrocarbons or of polymeric 2-chlorobutadiene-LS. It is to be understood that the term polyvinylchloride comprises also the products of the. after-chlorination thereofwhich are obtainable according to the process described in U. 8. PatentNo. 1,982,765 to Curt Schfinburg. The term esters of N-alkylaminocarboxylic acids" defines such tertiary amines wherein at least one ofthe radicals attached to the tertiary nitrogen atom bears the radical ofan alkylene carboxylic acid-ester. ents (if any) may be of the aromaticseries (for instance phenyl or naphthyl) or of the aliphatic As radicalsof carboxylic series such as butyl. acid esters those of acetic acidesters are-preferred. As alcohols which are contained in our newsofteners in the esterified state there may be mentioned glycolchlorohydrin', glycolmono alkyl ethers, butyl alcohols and higheraliphatic or hydroaromatic alcohols. A. preferred species within our newtype of softener asdeflned above is represented by the followingformula;

N (CHaCOOalkyl):

it being to be understood that the alkyl prefer-'- ably stands for oneof the alcohols defined above. Another species are represented by thefollowing formulae:

' aryl-N(QH:.COOR):,

alkyl-N(CH:.COOR )1 and aryl N-CH.C 0 0 R.

alkyl respect they are superior to the hitherto known softeners for suchmaterials, the softening capacity of which quickly decreases with adecrease of temperature. Contrarythereto. the elasticity and plasticityof plastic materials, shaped articles and the like prepared from thesaid halogen containing high molecular substances and our new softenersare always equally good within the whole range of temperature to whichsuch plas- 100 parts. of polyvinyl chloride are kneaded with 35 parts ofN butyl-N-phenyl-amino acetic The remaining substitu-' sile strengtheven hexyl ester. The mixture is then rolled out at acid butyl .esteruntil a homogeneous mixture has been reached. The mixture is then rolledout at 170. The resulting plasticmaterial shows excellent mechanicalproperties and an excellent .ten-

at low temperatures.

Example .2 g 100 parts of polyvinyl chloride are kneaded in the heatwith 50 parts of nitrilo triacetic acid iso- 120 and molded at 170. Theresulting articles are of a rubber-like character and shownconphosphate.

ester are worked on a kneader at 100 C. with 35 I parts of the esterof-glyeol mono-butylether and siderably increased elasticity,extensibility and stability towards cold when compared with thoseprepared from other softeners such as tricresyl Example 3 100' parts ofa mixed polymerizate of 0 vinyl chloride and 20% of acrylic. acid methylN-butylamino di(acetic acid). Homogenization of this mixture iseflected'by a 10 minutes working on the roller. On the calender therecan be obtained from such mixtures light-colored sheets of .arubber-like character, the elasticity of which is not materiallydecreased at a low temperature.

Example 4 A lacquer consisting of Parts Chlorinated rubber (of achlorine content of The ester of glycolmonobutylester and nitrilotriacetic acid elasticity even at a low temperature. In this 5 A'mixtureof toluene and xylene (1:1) 59 is applied onto an iron surface which isfreed from rust. After evaporation of the solvent an enamel-like coatingis obtained which is characterized by an excellent extensibility. Thechlorinated rubber can be replaced with an equal success by the productof the chlorination of a synthetic rubber, such as one prepared by theemulsion polymerization of butadiene and styrene.

The softener described above showsthe boiling point 240-250 at 1-2 mm.pressure.

We claim:

'1'. The composition of matter comprising a halogen containing highmolecular organic compound selected from the group consisting ofpolyvinyl chloride, mixed polymerizates of vinyl chloride and otherpolymerizable compounds, and chlorinated rubber, the high molecularhalogen containing compound having incorporated therewith a tertiaryamine containing at least one CH:.COO.alUl radical attached to thetertiary nitrogen atom.

2. The composition of matter comprising poly vinylehloride and anesterof the following formula:

N.(CI-Iz.COO.alkyl) a 3. The composition of matter comprisingpolyvinylchloride and a compound of the formula:

least two of the radicals attached to the tertiary groups represent-CH2.CO0.alkyl MAX B6GEMANN. JOHANNES NELLES.

